Stereoselective synthesis of beta-C-Allyl- and beta-C-propargyl-D-arabinofuranosides

TitleStereoselective synthesis of beta-C-Allyl- and beta-C-propargyl-D-arabinofuranosides
Publication TypeJournal Article
Year of Publication2008
AuthorsRamana, CV, Narute, SB, Gonnade, RG, Patil, RS
JournalSynthesis-Stuttgart
Issue11
Pagination1783-1787
Date PublishedJUN
ISSN0039-7881
KeywordsAllylation, Barbier reaction, C-glycoside, D-mannose, propargylation, Ring transposition
Abstract

The stereoselective synthesis of beta-configured C-allyl- and C-propargyl-D-arabinofuranosides (4,7-anhydro-1,2,3-deoxy-D-gluco-oct-1-enitols and -oct-1-ynitols) was addressed by employing allylation/propargylation of a dialdofuranose under aqueous Barbier reaction conditions and acid-catalyzed furan ring transposition of 5-O-mesyl-manno-oct-7-eno- or 5-O-mesyl-manno-oct-7-ynofuranoside derivatives.

DOI10.1055/s-2008-1067016
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.260

Divison category: 
Organic Chemistry